Vanessa from Kent is a receptionist at an insurance company. She gets the chance to choose between City Boy Thomas from Redmond and Country Boy Carl from Shelton. Thomas thinks he's got this one all wrapped up because he has passes to Watershed and a room at the Winery next store to the Gorge. He is going with a group of friends so she could join along. But it turns out Carl also has Watershed passes and he plans on camping out in General with just her. (By the way, we are all a little concerned because it seems like neither of these guys has ever been to Watershed, but everyone seems pretty stoked for it!) So Vanessa faces not just the choice of City Boy vs Country Boy, but also hotel room vs tent, and group date vs solo date, three hours from home. So which guy will she pick? And will they actually meet up? And will any of them use sunscreen?